My 50 First Dates Challenge: How I Un-Fucked My Life

This is my love story. The story of how I am learning to love myself. Love myself after a failed marriage. Love myself even though I’m in a situation I never thought I’d be in again. Love myself and grow through all of the ups and downs of online dating. Love myself and grant myself permission to do whatever it takes to have the experiences I need to evolve.

Fucking Lists

This story all started the night I made two lists. The first list contained all of the things I wanted to experience as a single woman. Things that I believed would help me get “Un-fucked”. I got married at the age of 20 when I became pregnant by the very first guy I had sex with. I stayed in a very unhappy and unfulfilling marriage for 15 years— you could say, I got fucked. And I had a lot of un-fucking to do!

The second list was the “Fuck-it” list, which is basically a bucket list containing every sexual act that I wanted to try before I considered settling down again. Discovering just how many things I had kept suppressed, and just how far away I had moved from being authentic was eye-opening.

Right after I made the lists, I experienced the strangest revelation. I had spent 15 years in a marriage where I felt incredibly alone, yet the longer I was single, and the more connected I got with what my wants and needs were, the less lonely I felt. So as a single woman, I felt less lonely than I ever had, and do you want to know why? Because I had missed the shit out of myself. I had been choosing my husband and he had been choosing himself, and there was nobody to choose me.

Well, it’s a brave new world now ladies, because I’ve committed to spending a whole year choosing me!

photo: by Josh Ness via Unsplash

The 50 First Dates Challenge

In a real effort to check all of the items off my lists, I decided that I would download Tinder and let the fun begin. Only it wasn’t as fun as I had imagined. I picked my best selfie and wrote what I thought was a great bio to let guys know I was looking for sexy time. It read:

Sometimes I like to think I’m a good person, but then I remember I’m on Tinder. But I’m just on here to make friends, just like I’m on Pornhub to watch the plumber fix the sink.

As my first date approached I was incredibly nervous and decided to do what I do best when nervous: channel my inner badass and swag it out! I flipped my hair over my shoulder, piled on the lip-gloss and strode into the restaurant!

It didn’t go great and neither did my next nine dates, so I deleted Tinder and decided I was done.

A week went by and I realized that I probably didn’t give the app a fair enough shake, and that I should really make a commitment if I wanted to see my process through. So I once again took a selfie and wrote a new bio. My new bio read:

After a series (9 and 1/2) of misfortunate first dates (after the last one I hastily deleted Tinder—you know who you are weirdo!) I decided that perhaps I just wasn’t ready for the big bad world of dating. Then I thought to myself, ‘If I can’t beat them, maybe I should join them by writing a memoir of 50 first dates, Tinder-style!’

It could be just like the movie, except completely unromantic, without the amnesia or true love, and without a happy ending! So, I’m going to go on 50 first dates before I delete this again….wanna be a character in my new book? P.S. I work in Special Education, if you would have ever required my services, please swipe LEFT. It’s totally not personal, a girl just needs some variety, ya know?

What started as a joke actually became a really fun journaling exercise. After each date I would come home, write a character synopsis and yelp review, as well as what I had learned about myself. I started taking the whole dating thing a lot less seriously and started focusing on how much fun it could all be. I also decided that I was ready to come into my own as a sexual being and really truly rock my inner-dirty girl, and decided anyone who reeled back was simply not my people!

The added bonus of taking accountability for my own sexuality was an intense connection with my femininity and a higher understanding of who I am and how I show up in relationships. I’m only halfway through my journey of 50 first dates and still have an incredible amount of growing left to do. But I’m allowing myself to experience all of the good, bad, sexy, and ugly.

Because of just how very fragile the male ego can be, I’ve decided it’s in everyone’s best interest for all names to be changed, but otherwise, the following reviews reflect my honest experience.

The 50 First Dates: Part 1

Date 1. Dan, Dan the paint man

Synopsis:Average is the nondescript word that comes to mind when concocting a way, to sum up the 40-year-old male commercial paint salesman. Average in height, weight, dress, speech, intelligence, and appeal. It seems that Dan has found a way to turn complaining into a currency that he uses in an attempt to stay relevant. He is absolutely one of the most easily forgettable people you could meet.

Yelp review:Although Dan was a nice enough guy, there really just wasn’t any chemistry. His negativity seemed to pour off of him in waves and made for a very long evening. I now know everything there is to know about the in’s and out’s of the commercial paint industry, as well as just how awful his ex-wife Nancy is. Needless to say, I did not accept the offer of a second date. Overall I would give Dan Dan the paint man: 2 stars⭐⭐

What I learned about myself:I now know that I have the ability to put my big girl panties on, suck it up and put myself out there. I was terrified about whether or not I would be able to get back on the proverbial dating horse again. My marriage and subsequent divorce had both really taken a toll on my self-esteem. It’s not so much that dating is a way to seek validation, but I do think it’s somewhat typical for a woman to feel perhaps some validation from having and keeping the attention of a male she finds attractive. I’m going to certainly be exploring my relationship with seeking validation, and my own self-worth during this process of dating. I want to feel sexy and attractive for myself, not for male attention, however, I will be seeking male attention through the process of dating, so I certainly hope to find a balance that feels authentic for myself.

Date 2. Liam the man of many words

Synopsis:Incredibly interesting and engaging right out of the gate. Liam is the kind of man that is almost on a professional level with his ability to engage a woman and put her at ease. Well traveled, with a fascinating tapestry of experiences, he had recently decided to trade in corporate America in the pursuit of something that set his soul on fire: becoming a pilot. Standing at nearly 6 feet with Italian lineage—he is tall, dark, and handsome. Although he has never been married, has no children, and is in his late 30’s, he is still active in his search for connection. An expert at sexting—saying things that could make Hugh Hefner blush—Liam is simply a fun time.

Yelp Review:Liam and I met for tea in a trendy shop downtown. We had a pleasant conversation that flowed naturally. Although the experience was comfortable, there was very little chemistry in person. Overall I would give Liam: 4 stars ⭐⭐⭐⭐

What I learned about myself:I now know just how exciting the rush of staying up all night talking to a guy on the phone can be as an adult. It feels like being a teenager all over again! I also was able to cross sexting √ and phone sex off of my list √ which was way less awkward than I had imagined. It was interesting to me how real the chemistry could feel over the phone, and then how flat-lined it could feel in real life. I mean who knew?!

Date 3. John the meathead

Synopsis:Hello biceps! A gentle giant of a man, standing at 6-foot-four, who can turn any life experience into a boxing analogy. A real-life romantic, John has been unlucky in love but has not allowed it to change his goal of finding true love. He’s perhaps a bit rough around the edges and not one for deep conversation, but he can bench press 300 lbs. Sandy brown hair, blue eyes, and a killer smile make it easy to overlook the fact that he struggled with the math required to figure out the tip.

Yelp Review:John is a perfect gentleman who any girl would be lucky enough to snag a date with. Although he may not be a Merit scholar, I’m willing to bet that if you were interested in wall sex, he would be your guy. Charming and funny, he is a man’s man kind of guy. Overall I would give John: 4 Stars ⭐⭐⭐⭐

What I learned about myself:

When I started this process I was determined to discover what my “type” is, and I now know that my type has nothing to do with physical appearance. I’ll readily admit that I’d fuck an ugly guy if he were super smart. When a man can challenge me intellectually, I literally get turned on. I’m not even kidding right now. What I learned through this date is that I am a sapiosexual. A sapiosexual is someone who finds sexual stimulation from the way a person’s mind works. It means you literally are attracted to intelligence. Looks take a backseat to a person’s wit.

Date 4. Chase the attorney

Synopsis:Chase may be one of the most self-important people on the planet. An attorney who is a straight-to-the-point kind of guy, who feels like time is money and neither should be wasted. Lacking interpersonal skills, with a double helping of intellect, making him a rather unbalanced individual. He’s a man who walks in the middle of a hallway, sidewalk, or other shared walking space, forcing other people to move out of his self-important way.

Yelp review:When I jokingly refer to having been on 27 and 1/2 first dates, my date with Chase is what I refer to as my half date. Within the first 15 minutes of the date, he asked me how I feel about strangulation and rope play, to which I replied, “Yes, having a stranger I just met online choke and suspend me sounds like very smart plan, let’s go now!”

Just kidding! I got up and left, making it only a half date as far as I’m concerned. Overall I would give Chase: 0 stars

What I learned about myself:I learned that intellect alone is not enough to get my motor going! I also learned that even though someone seems “normal” during days of conversing back and forth on a dating app, does not equate to a “normal” meeting experience. While I do appreciate a man who can be clear and upfront with their expectations, I also require just a little bit of finesse as well. This opportunity also provided me with the ability to really look at what my “hard limits” might actually be. It’s easy to fantasize about sexual proclivities, but quite another thing when faced with the real opportunity. Although I think I would be up for some bondage play, I realized that for me, it would require a certain level of trust for my potential partner. Something I still feel a need to get clear on is why I get so uncomfortable talking about sexual things, am I a prude? If so, do I want to continue to be? Something to examine and work through!

Date 5. Joshua tree

Synopsis:Half man, half tree climbing god, 100% delicious! A gentle soul transplanted from Arizona, who spends his day cutting down tree limbs that obstruct power lines. At the age of 38 he has recently decided that he is ready to look for a partner and Tinder is most certainly the place to do so. He loves dogs, hates cats, and only drinks socially. A great conversationalist who kept things rather PG for the most part.

Yelp review:Of all of my dates, this one has been the one I was most unsure about. Joshua, although a very kind guy, was very murky about what he actually wanted out of the experience. Dinner was a little awkward and just felt off, like neither one of us was willing to go out on a limb first and just throw caution to the wind. Eventually, it was me who made it clear that I was looking for a FWB (friends with benefits) situation. Poor Joshua Tree was disappointed, as he was certain he was looking for love. Overall I would give Joshua 2 ⭐⭐

What I learned about myself:

I learned that while I don’t want to close myself off to the possibility of love at some point, I am simply not ready for love at all right now. I am very clear that I am looking for an opportunity to explore my ability to engage in a relationship and explore my sexuality with someone, but have no desire to field an invitation to Thanksgiving or to meet anyone’s kids or family.

I’m giving myself permission to ask for what I want and to not feel guilty or obligated if that doesn’t line up with someone else’s agenda. Just like I won’t judge someone else for being where they are, I also won’t judge myself for being where I am. This is my journey and my process and I’m absolutely committed to seeing it through and honoring where I’m at during each step. I’m learning to love myself and show up for myself without doubt and judgment, but holy fuck is it a difficult process to fight these internal voices that lie and say I’m not enough or that I don’t measure up, and who am I to turn someone else away, what if nobody else wants me…

Well, fuck that—I want me!

Stay tuned for the next installment of 50 First Dates. Let’s just say, things heat up.

I love this idea! It reminds me of Maria Headly’s book, “The Year of Yes,” where she said yes to every date she was asked on for a year. She met some interesting characters living in New York City. I’m sure you will too!

[…] about how my adventure started with two lists (the Fuck-It list and the Get Un-Fucked list), in my previous article. It also reveals how I came to the decision to write a character synopsis, yelp review, and what I […]

[…] I recently decided that reentering the dating world, after the disintegration of my 15-year marriage, wasn’t humbling enough. I thought I could really step up my game by also writing and sharing a “tell-all memoir” documenting my process. I’m sure it sounds odd to hear that I am on a journey of self-discovery through the most unlike source—online dating—but I really truly am committed to finding myself during this adventure! You can read about how my adventure started with two lists (the Fuck-It list and the Get Un-Fucked list), and has pogressed up until now here. […]

[…] I recently decided that reentering the dating world, after the disintegration of my 15-year marriage, wasn’t humbling enough. I thought I could really step up my game by also writing and sharing a “tell-all memoir” documenting my process. I’m sure it sounds odd to hear that I am on a journey of self-discovery through the most unlike source—online dating—but I really truly am committed to finding myself during this adventure! You can read about how my adventure started with two lists (the Fuck-It list and the Get Un-Fucked list) and has progressed up until now here. […]

[…] I recently decided that reentering the dating world, after the disintegration of my 15-year marriage, wasn’t humbling enough. I thought I could really step up my game by also writing and sharing a “tell-all memoir” documenting my process. I’m sure it sounds odd to hear that I am on a journey of self-discovery through the most unlike source—online dating—but I really truly am committed to finding myself during this adventure! You can read about how my adventure started with two lists (the Fuck-It list and the Get Un-Fucked list) and has progressed up until now here. […]

[…] I recently decided that reentering the dating world, after the disintegration of my 15-year marriage, wasn’t humbling enough. I thought I could really step up my game by also writing and sharing a “tell-all memoir” documenting my process. I’m sure it sounds odd to hear that I am on a journey of self-discovery through the most unlikely source—online dating—but I really truly am committed to finding myself during this adventure! You can read about how my adventure started with two lists (the Fuck-It list and the Get Un-Fucked list) and has progressed up until now here. […]